Phenethylamines
Phenethylamines represent a wide class of molecules with psychoactive stimulant Description
activity
which
includes
amphetamine,
methamphetamine
and
3,4methylenedioxymethamphetamine (MDMA, also known as ecstasy), molecules that
are controlled by the Convention of 1971. They are divided into different sub-groups
according to the different substitution on the aromatic ring, on the alkyl chain and
on the nitrogen and are identified for most of numbers and letters: the series "2C" is
characterized by replacing 2,5-dimethoxy, the series "D" (DOI , DOC), is analogous to
the series 2C, but has a methyl on the chain, the series "NBOMe", with several
examples recently appeared on the market of drugs, are phenethylamines that see
the nitrogen atom substituted with a 2-methoxybenzylic group. These structural
variations give the phenethylamines effects that vary from the stimulating effects to
hallucinogenic type, such analogs of mescaline, a phenethylamin of natural origin,
which belongs to the "2C" series.
Phenethylamines are sold in tablets of various colors/shapes, capsules,
powder/crystals. Recently in Italy has been recorded numerous seizures of
phenethylamines of the "NBOMe"
series in the form of "blotters", typical
formulation of highly potent hallucinogens.
Some phenethylamines registered by the National Early Warning System from 2010,
are herein reported: 25I-NBOMe, la 2C-B, la 2C-H, la 2C-E, la DOB, la DOC, la 4-FA, la
4-MA, la PMA e la PMMA.
Chemicla structures of some phenethylamins registerd by the National Early Warning System.
NAME
RN
Rα
Rβ
R2
R3
R4
R5
R6
Phenethylamine
H
H
H
H
H
H
H
H
Amphetamine
H
CH3
H
H
H
H
H
H
Methamphetamine
CH3
CH3
H
H
H
H
H
H
PMA
H
CH3
H
H
H
CH3
H
H
PMMA
CH3
CH3
H
H
H
CH3
H
H
4-MA
H
CH3
H
H
H
CH3
H
H
4-FA
H
CH3
H
H
H
F
H
H
DOC
H
CH3
H
OCH3
H
Cl
OCH3
H
DOB
H
CH3
H
OCH3
H
Br
OCH3
H
DOI
H
CH3
H
OCH3
H
I
OCH3
H
2C-H
H
H
H
OCH3
H
H
OCH3
H
2C-C
H
H
H
OCH3
H
Cl
OCH3
H
2C-B
H
H
H
OCH3
H
Br
OCH3
H
2C-E
H
H
H
OCH3
H
CH2CH
3
OCH3
H
25H-NBOMe
BOMe
H
H
OCH3
H
H
OCH3
H
25I-NBOMe
BOMe
H
H
OCH3
H
I
OCH3
H
Note: BOMe=(2-methoxyphenyl)methyl
Phenethylamines is a very large group of substances therefore their pharmacological Potency
activity and their potency varies from product to product. Phenethylamines of
amphetamine-type (MDMA or ecstasy, amphetamine and methamphetamine), have
stimulating activity and circulate generally in the form of tablets of various color, and
logos, while phenethylamines recently appeared on the territory, belonging to the
series of the so-called "NBOMe," have hallucinogenic effects and circulating in the
form of "blotters" similar to those of LSD, as extremely potent at very low doses.
Phenethylamines are reported to be ingested, snorted, and more recently taken Assumption
sublingually (blotters). The phenethylamines cause an increase in heart rate, and effects
respiration, blood pressure and body temperature; the latter effect can cause
seizures and coma. One of the most dangerous effects of this type of drugs is the
muscle stiffness. The effects, however, varies from substance to substance, and
include for example for 2C-I, very high blood pressure associated with seizures,
confusion; for the 2B-B, cardiovascular disorders, dehydration, confusion; for 2C-T,
depression of the central nervous system, panic attacks, vomiting, delirium, loss of
memory; for 2C-T-2, panic attacks, paranoia, muscle rigidity, vomiting, anxiety; for
2C-T-7, vomiting, headache, confusion, delirium, high blood pressure, muscle
spasms.
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Photos
of
some
products
notified
to
the National
Early Warning
System
and
resulted
to
contain
phenetylamin
es
Since 2010, in Italy, there have been 4 cases (aged 16 and 39 years) of acute
intoxication by phenethylamines. Two cases were related to the assumption of
PMA/PMMA with symptoms such as agitation, confusion, hallucinations, sweating,
mydriasis, hyperemia, tachycardia, normothermia. One intoxication related to 2C-E
consumption and one to 2C-B consumption, with presentation of symptoms such as
mydriasis, delirium, agitation, tachycardia, coma, convulsions. The cases were
registered in Liguria (2 cases), Umbria and Veneto.
Intoxication
cases
registered in
Italy
In Italy, the following phenethylamines are illegal (Tables of the Law on the Legal status
regulation of narcotic drugs and psychotropic substances, prevention, treatment and
rehabilitation of drug addiction Presidential Decree 309/90 as amended): 2C- B, 2C- I,
2C-T-2, 2C-T-7, 4-MTA, amphetamine, DMA, DOB, DOET, DOM, MBDB, MDA, MDEA,
MDE, MDMA, methamphetamine, MMDAN-ethylamphetamine, N-hydroxy-MDA,
PMA, PMMA, TMA, TMA-2. More recently there have been placed under control
other molecules: 4-methylamphetamine (4-MA) and 4-fluoroamphetamine (4-FA)
(Decree of October 24, 2012, OJ 264 of 12/11/2012 ). Have also been brought under
control molecules 5-IT (Decree of December 10, 2012, OJ No. 303 of 31/12/2012)
and 6-APB, 5-APB, 6-APDB, 5-APDB (Decree of 25 June 2013, OJ No. 158 of
08.07.2013), which despite being indole derivatives (the 5-IT) or benzofuran
derivatives, they have a phenethylamines basic skeleton.
Amphetamine, methamphetamine and ecstasy are detected with normal screening
tests on urine, like other traditional drugs, as well as other structural analogues may
give positivity to such tests. The other phenethylamines are instead not easily
detectable to the normal screening test but are subsequently detected through
blood tests and urine tests conducted in the laboratory. In case of positivity to these
substances driving a car, motorcycle or scooter, the law enforcement may withdraw
the license, impound the vehicle, impose fines, make report to the Prefecture, pick up
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your passport.
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